TWI468491B - Electroluminescent device using electroluminescent compounds - Google Patents

Description

Electroluminescent device using electroluminescent compound

This invention relates to electroluminescent devices comprising electroluminescent compounds.

In the display device, the electroluminescent device (EL device) is a self-luminous display device, which exhibits the following advantages over the LCD: wide viewing angle, excellent contrast, and fast response rate.

The EL device is classified into an inorganic EL device and an organic EL device depending on the material for forming the light-emitting layer and the light-emitting mechanism. Among them, in terms of luminous efficiency, color purity, and operating voltage, the organic EL device has a high advantage, so that a full color display can be easily realized.

At the same time, Eastman Kodak developed an organic EL device in 1987 that used low-molecular-weight aromatic diamines (as materials for forming EL layers) and aluminum complexes for the first time [Appl. Phys. Lett. 51,913 , 1987].

EL materials can be classified as host materials and dopant materials according to their functionality. It is generally known that an EL layer can be prepared by doping a dopant onto a host material, thereby fabricating a device structure having optimum EL properties. Recently, in view of the EL characteristics required for medium to large OLED panels, it is imperative to develop EL devices having high efficiency and long life, and particularly urgently to develop materials having EL characteristics far superior to those of conventional EL materials. The desired properties of the host material (as a solid solvent and energy transporter) are high purity and a suitable molecular weight to enable vapor deposition in a vacuum state. In addition, it should have a high glass transition temperature as well as a thermal decomposition temperature to ensure thermal stability. Furthermore, the host material should have high electrochemical stability to provide long life. It can easily form an amorphous film with high adhesion to other adjacent materials without interlayer migration.

The most important factor determining the luminous efficiency of an Organic Light-Emitting Diode (OLED) is the type of electroluminescent material. Up to now, although fluorescent materials have been widely used as electroluminescent materials, in view of the electroluminescence mechanism, the development of phosphorescent materials is one of the best methods for theoretically improving luminous efficiency by a factor of four.

To date, ruthenium (III) complexes have been widely known as phosphorescent materials, including (acac) Ir(btp) ₂ , Ir(ppy) ₃ and Firpic as red, green and blue phosphorescent materials, respectively. In particular, many phosphorescent materials have been studied in Japan, Europe, and the United States in the near future, and it is expected that a further improved phosphorescent material will be developed.

As for the host material of the phosphorescent light emitting material, 4,4'-N.N'-dicarbazole-biphenyl (CBP) is by far the most widely known and has a hole blocking layer applied thereto ( For example, BCP and BAlq) high efficiency OLEDs have also been developed. Companies such as East-North Pioneer (Japan) have published several kinds of bis(2-methyl-8-hydroxyquinoline) (p-phenylphenol) aluminum (III) (bis(2-methyl-8-quinolinato) (p-phenylphenolato)aluminum (III)) (BAlq) and its derivatives are high-performance OLEDs developed as a host material for phosphorescent materials.

While the materials of the prior art have advantages in light emitting properties, they are subject to variations during high temperature vapor deposition in vacuum because of their low glass transition temperature and very poor thermal stability. In an organic electroluminescent device, power efficiency = (π / voltage) × current efficiency is defined. Therefore, the power efficiency is inversely proportional to the voltage, and in order to achieve lower OLED power consumption, the power efficiency should be higher. In fact, OLEDs using phosphorescent electroluminescent (EL) materials exhibit significantly higher current efficiencies (candle (cd) / ampere (A)) than OLEDs using fluorescent EL materials. However, in the case of using a conventional material (for example, BAlq and CBP) as a host material of a phosphorescent material, since it has a higher operating voltage than an OLED using a fluorescent material, power efficiency (lumen (1 m)) / watt (w)), it did not receive any significant advantage.

In general, the organic electroluminescent device is basically provided in the form of a laminate formed of an anode/organic EL layer/cathode, which is suitably equipped with a hole injection transport layer and an electron injection layer; for example, Known as the following structure: anode / hole injection layer / hole transport layer / organic EL layer / cathode; anode / hole injection layer / hole transport layer / organic EL layer / electron injection layer / cathode; and anode / electricity Hole injection layer / hole transport layer / organic EL layer / electron transport layer / electron injection layer / cathode, and the like.

A variety of organic compounds can be used in the electron injecting layer or electron transporting layer of the device in the form of a laminate. These compounds comprise a photo-metal complex as shown below: tris(8-quinolinolate)aluminum (Alq ₃ ), Diazole, triazole, benzimidazole, benzo Oxazole, benzothiazole, etc., but these compounds are not completely satisfactory in terms of EL luminescence, durability, and the like. Among them, Alq _{3 has} been reported as the best compound with excellent stability and high electron affinity. However, when it is used in a blue electroluminescence device, color purity is lowered by luminescence due to diffusion of excitons.

As described above, recent advances in the commercialization of electroluminescent devices have been remarkable, and are characterized in that a high-luminous thin EL device having a low applied voltage, a plurality of EL wavelengths, and a fast response is obtained, and low power consumption is high efficiency. A long-life device is required.

Accordingly, it is an object of the present invention to provide an electroluminescent device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode; wherein the organic layer A divalent or trivalent metal complex as a host material, and a plurality of electroluminescent dopants are included.

Another object of the present invention is to provide an electroluminescent device which exhibits excellent luminous efficiency, high color purity, low operating voltage, and good operational life.

Specifically, the electroluminescent device of the present invention includes: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode; and the organic layer includes one or more The organic electroluminescent compound represented by the chemical formula (1) is used as a host material:

Chemical formula (1)

L ¹ L ² M(Q) _y

Wherein the ligands L ¹ and L ² are independently selected from the following structures:

Wherein M represents a divalent or trivalent metal;

When M is a divalent metal, y is 0; and when M is a trivalent metal, y is 1;

Q represents (C6-C60) aryloxy or tri(C6-C60)aryldecylalkyl, and the aryloxy or triarylsulfanyl group of Q may be further substituted by (C1-C60)alkyl or (C6-C60) Substituted by an aryl group; X represents O, S or Se; ring A and ring B independently represent a 5- or 6-membered heteroaryl ring, or a 5- or 6-member heteroaryl fused to a (C6-C60) aromatic ring. Ring; Ring A may form a chemical bond with R ₁ to form a fused ring, and Ring A or Ring B may be further substituted with one or more substituents selected from the group consisting of: (C1-C60)alkyl, halogen, halogen Substituted (C1-C60) alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl (C6-C30) An aryl decyl group, a tri(C6-C30) aryl decyl group, a di(C1-C30)alkylamino group, and a di(C6-C30) arylamine group; R ₁ to R ₇ independently represent hydrogen, (C1-C60)alkyl, halogen, (C1-C60)alkyl having a halogen substituent, tri(C1-C30)alkyldecane, di(C1-C30)alkyl(C6-C30)aryldecane , tris(C6-C30)aryldecyl, (C6-C60)aryl, (C4-C60)heteroaryl, di(C1-C30)alkylamino and di(C6-C30)arylamine group; or R ₁ to R ₇ may be respectively via an alkylene group or Alkenyl group bonded to an adjacent substituent to form a fused ring; and a substituent in ring A or ring B of the aryl group or heteroaryl group, or R ₁ to R ₇ of the group aryl, heteroaryl, or R ₁ to R ₇ are formed of the fused ring may be further substituted with one or more groups selected from the substituents via alkylene or alkenylene group linking to an adjacent substituent groups: (C1-C60) alkyl , halogen, cyano group, (C1-C60) alkyl group having a halogen substituent, (C3-C60) cycloalkyl group, (C1-C30) alkoxy group, (C6-C60) aryl group, (C4-C60) Heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl,di(C1-C30) An alkylamino group and a di(C6-C30)arylamino group.

Referring now to the drawings, FIG. 1 is a schematic cross-sectional view of an OLED including a glass 1, a transparent electrode 2, a hole injection layer 3, a hole transport layer 4, an electroluminescent layer 5, an electron transport layer 6, and an electron injection layer. 7 and an aluminum (Al) cathode 8.

The term "alkyl" or "alkoxy" as used herein, includes both alkyl and alkoxy groups, both straight and branched.

The term "heteroaryl ring" as used herein means a 5- or 6-membered aromatic ring containing one or more heteroatoms selected from N, O and S, and includes, for example, pyrrole, pyrazole, Azole Oxazole, thiazole, isothiazole, imidazole, Diazole, thiadiazole, pyridine, pyridyl Pyrimidine and pyrene . Specific examples of the 5- or 6-membered heteroaryl ring fused to the (C6-C30) aromatic ring include: carbazole, benzo Oxazole, benzothiazole, benzimidazole, anthracene Quino Quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, quinoline, and isoquinoline. Ring A is preferably selected from Oxazole, thiazole, imidazole, Diazole, thiadiazole, benzo Oxazole, benzothiazole, benzimidazole, pyridine and quinoline. The ligands L ₁ and L ₂ are independently selected from the following structures:

Wherein X, R ₁ , R ₂ , R ₃ and R ₄ are as defined in the formula (1); Y represents O, S or NR ₂₄ ; R ₁₁ to R ₂₃ independently represent hydrogen, (C1-C60) Alkyl, halogen, (C1-C60)alkyl having a halogen substituent, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecane, di(C1- C30) alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, di(C1-C30)alkylamino or di(C6-C30)arylamine; or R ₁₃ To R ₁₆ and R ₁₇ to R ₂₀ may be bonded to an adjacent substituent via an alkylene or an extended alkenyl group, respectively, to form a fused ring; and the fused ring may be substituted with one or more substituents selected from the group consisting of Substitution: (C1-C60)alkyl, halogen, cyano, (C1-C60)alkyl having a halogen substituent, (C3-C60)cycloalkyl, (C1-C30) alkoxy, (C6-C60 Aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, bis(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryl a decyl group, a di(C1-C30)alkylamino group, and a di(C6-C30)arylamino group; R ₂₄ represents a (C1-C60)alkyl group or a (C6-C60)aryl group; and R ₁₁ to R ₂₄ The aryl or heteroaryl group may be further selected by one or more Substituted by the following substituents: (C1-C60)alkyl, halogen, cyano, (C1-C60)alkyl having a halogen substituent, (C3-C60)cycloalkyl, (C1-C30) alkoxy (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, bis(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6) -C30) arylalkyl, di(C1-C30)alkylamino and di(C6-C30)arylamine.

The ligands L ¹ and L ² are independently selected from the following structures:

Wherein X is as defined in the formula (1); R ₁ to R ₇ independently represent hydrogen, (C1-C60)alkyl, halogen, (C1-C60)alkyl having a halogen substituent, and three (C1) -C30) alkyl nonyl, di(C1-C30)alkyl(C6-C30)aryldecyl, tris(C6-C30)aryldecyl, (C6-C60)aryl, (C4-C60) a heteroaryl group, a di(C1-C30)alkylamino group or a di(C6-C30)arylamino group; R ₁₁ to R ₂₃ independently represent hydrogen, (C1-C60)alkyl, halogen, halogen substituted (C1-C60)alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, bis(C1-C30)alkyl (C6-C30) An arylalkylene group, a tris(C6-C30)aryldecylalkyl group, a di(C1-C30)alkylamino group or a di(C6-C30)arylamino group; R ₂₄ represents a (C1-C60)alkyl group, (C6-C60) aryl or (C4-C60) heteroaryl; R ₂₅ to R ₃₂ independently represent a hydrogen system, (C1-C60) alkyl, halo, cyano, halo substituent having a group of (C1-C60 An alkyl group, (C3-C60) cycloalkyl group, (C1-C30) alkoxy group, (C6-C60) aryl group, (C4-C60) heteroaryl group, tri(C1-C30)alkyl decyl group, Di(C1-C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, di(C1-C30)alkylamine And di- (C6-C30) aryl group; R ₁ through R _7, R ₁₁ to R _23, R _24, and R ₂₅ to R ₃₂ of the aryl group or heteroaryl group may be further substituted with one or more substituents selected from Substituted by the following substituents: (C1-C60)alkyl, halogen, cyano, (C1-C60)alkyl having a halogen substituent, (C3-C60)cycloalkyl, (C1-C30) alkoxy (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, bis(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6) -C30) arylalkyl, di(C1-C30)alkylamino and di(C6-C30)arylamine; and the alkyl group may be a straight or branched chain.

In the chemical formula (1), M represents a divalent metal selected from the group consisting of Be, Zn, Mg, Cu, and Ni, or a trivalent metal selected from the group consisting of Al, Ga, In, and B; The Q system is selected from the following structures:

When M is a divalent metal, the compound represented by the chemical formula (1) can be specifically exemplified by the following compounds, but is not limited thereto:

Wherein X represents O, S or Se; M represents Be, Zn, Mg, Cu or Ni; R ₁ to R ₇ independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl , isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecane Base, fluorine, chlorine, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, trimethyldecyl, triethyldecyl, tripropyldecyl, three (t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyldecyl, triphenyldecyl, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridine Base, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo An azolyl, dimethylamino, diethylamino or diphenylamino group; R ₁₁ to R ₂₃ independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl , fluorine, chlorine, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tri Tertiary butyl) decyl, tert-butyldimethylmethyl, dimethylphenyl decyl, triphenyl decyl, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl , quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo Azyl, dimethylamino, diethylamino or diphenylamino; R ₂₄ represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl , n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, phenyl, biphenyl, Naphthyl, anthracenyl or fluorenyl; R ₂₅ to R ₃₂ are independently represented by hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl Base, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, fluoro, chloro, cyano, trifluoromethyl Base, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, methoxy, B Oxyl, butoxy, hexyloxy, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo Azyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyldecyl, three a phenyl fluorenyl group, a dimethylamino group, a diethylamino group or a diphenylamino group; and the phenyl group of R ₁ to R ₇ , R ₁₁ to R ₂₃ , R ₂₄ , and R ₂₅ to R ₃₂ , Biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azolyl, benzofuranyl, benzothiazolyl, benzimidazolyl or benzo The azole group may be further substituted with one or more substituents selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso Pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, fluoro, chloro, cyano, trifluoromethyl, all Fluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, methoxy, ethoxy, Butoxy, hexyloxy, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo Azyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyldecyl, three Phenylalkyl, dimethylamino, diethylamino and diphenylamino.

When M is a trivalent metal, the compound represented by the chemical formula (1) of the present invention can be specifically exemplified by the following compounds, but is not limited thereto:

Wherein X represents O, S or Se; M represents Al, Ga, In or B; Q represents (C6-C60) aryloxy or tri(C6-C60)aryldecylalkyl, and the aryloxy group of Q or The triarylsulfonyl group may be further substituted by (C1-C60)alkyl or (C6-C60)aryl; R ₁ to R ₇ independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-Butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, Hexadecyl, fluorine, chlorine, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, trimethyldecyl, triethyldecyl, tripropyldecane , tris(t-butyl)decylalkyl, tert-butyldimethylmethylalkyl, dimethylphenyldecyl, triphenylsulfanyl, phenyl, biphenyl, naphthyl, anthryl, anthracene Base, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo An azolyl, dimethylamino, diethylamino or diphenylamino group; R ₁₁ to R ₂₃ independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl , fluorine, chlorine, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tri Tertiary butyl) decyl, tert-butyldimethylmethyl, dimethylphenyl decyl, triphenyl decyl, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl , quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo Azyl, dimethylamino, diethylamino or diphenylamino; R ₂₄ represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl , n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, phenyl, biphenyl, Naphthyl, anthracenyl or fluorenyl; R ₂₅ to R ₃₂ are independently represented by hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl Base, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, fluoro, chloro, cyano, trifluoromethyl Base, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, methoxy, B Oxyl, butoxy, hexyloxy, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo Azyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyldecyl, three a phenyl fluorenyl group, a dimethylamino group, a diethylamino group or a diphenylamino group; and the phenyl group of R ₁ to R ₇ , R ₁₁ to R ₂₃ , R ₂₄ , and R ₂₅ to R ₃₂ , Biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azolyl, benzofuranyl, benzothiazolyl, benzimidazolyl or benzo The azole group may be further substituted with one or more substituents selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso Pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, fluoro, chloro, cyano, trifluoromethyl, all Fluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, methoxy, ethoxy, Butoxy, hexyloxy, phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, pyridyl, quinolyl, furyl, thienyl, thiazolyl, imidazolyl, Azyl, benzofuranyl, benzothiazolyl, benzimidazolyl, benzo Azyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyldecyl, three Phenylalkyl, dimethylamino, diethylamino and diphenylamino.

The compound represented by the chemical formula (1) of the present invention is preferably selected from the following compounds, but is not limited thereto:

The electroluminescent device of the present invention is characterized in that the organic layer comprises an electroluminescent layer comprising: one or more electroluminescent compounds represented by the chemical formula (1) as an electroluminescent host material, and one or A plurality of electroluminescent dopants are present in an amount of from 1 to 20% by weight. The electroluminescent dopant to be applied to the electroluminescent device of the present invention is not particularly limited, but can be exemplified by the compound represented by the chemical formula (2):

Chemical formula (2)

M ¹ L ³ L ⁴ L ⁵

Wherein, M ¹ is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15, and Group 16 of the periodic table, And the ligands L ³ , L ⁴ and L ⁵ are independently selected from the following structures:

Wherein R ₆₁ to R ₆₃ independently represent a hydrogen (C1-C60) alkyl group having or not having a halogen substituent, and a (C6-C60) aryl group having or not having a (C1-C60) alkyl substituent; Or a halogen; R ₆₄ to R ₇₉ independently represent hydrogen, (C1-C60)alkyl, (C1-C30)alkoxy, (C3-C60)cycloalkyl, (C2-C30)alkenyl, ( C6-C60) aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, SF ₅ , tri(C1-C30)alkyldecyl, di(C1 -C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, cyano or halogen; or R ₇₀ to R ₇₆ may be alkyl (C2-C12) or C2-C12) an alkenyl group bonded to an adjacent substituent to form a fused ring or a multi-fused ring; and the alkyl, cycloalkyl, alkenyl or aryl group of R ₆₄ to R ₇₉ Or the fused or polycondensed ring formed by R ₇₀ and R ₇₆ via an alkyl or alkenyl linkage may be further selected from one or more selected from the group consisting of (CI-C60) alkyl, (C6- C60) aryl and a substituent of a halogen are substituted; R ₈₀ to R ₈₃ independently represent hydrogen, (C1-C60)alkyl with or without a halogen substituent, or with or without (C1- C60) an alkyl substituent (C6-C60) aryl; R ₈₄ and R ₈₅ independently represent hydrogen, a straight or branched chain (C1-C60) alkyl, (C6-C60) aryl or halogen; Or R ₈₄ and R ₈₅ may be bonded via an (C3-C12)alkylene group or a (C3-C12)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; And the alicyclic ring or the monocyclic ring formed by R ₈₄ and R ₈₅ of the alkyl group, the aryl group, or R ₈₄ and R ₈₅ via a (C3-C12)alkylene group or a (C3-C12)alkylene group. Or a polycyclic aromatic ring which may be further substituted by one or more substituents selected from the group consisting of straight or branched chain (C1-C60) alkyl groups with or without a halogen substituent, (C1-C30) Alkoxy, halogen, tri(C1-C30)alkyldecyl, tris(C6-C30)aryldecyl and (C6-C60)aryl; R ₈₆ represents (C1-C60)alkyl, (C6- C60) aryl, (C5-C60)heteroaryl or halogen; R ₈₇ to R ₈₉ independently represent hydrogen, (C1-C60)alkyl, (C6-C60)aryl or halogen, and R ₈₆ to R The alkyl or aryl group of ₈₉ may be further substituted by halogen or (C1-C60)alkyl; and z represents Wherein R ₁₀₁ to R ₁₁₂ independently represent hydrogen, (C1-C60)alkyl group having or without a halogen substituent, (C1-C30) alkoxy group, halogen, (C6-C60) aryl group, cyanide Or a (C5-C60)cycloalkyl group, or R ₁₀₁ to R ₁₁₂ may be bonded to an adjacent substituent via an alkyl or alkenyl group, respectively, to form a (C5-C7) spiro ring or a (C5-C9) thick Ring-bonded, or R ₁₀₁ to R ₁₁₂ may be bonded to R ₆₇ or R ₆₈ via an alkyl or alkenyl group to form a (C5-C7) fused ring.

In the chemical formula (2), M ¹ may be selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag, and is represented by the chemical formula (2). L ³ , L ⁴ and L ^{5 of the} compound may be independently selected from the following structures, but are not limited thereto.

Wherein R ₆₄ to R ₇₉ independently represent hydrogen, (C1-C60)alkyl, (C1-C30)alkoxy, (C3-C60)cycloalkyl, (C2-C30)alkenyl, (C6- C60) aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, SF ₅ , tri(C1-C30)alkyldecyl, di(C1-C30 An alkyl (C6-C30) aryl decyl group, a tri(C6-C30) aryl decyl group, a cyano group or a halogen; the alkyl group, cycloalkyl group, alkenyl group or aryl group of R ₆₄ to R ₇₉ may be further Substituted by one or more substituents selected from the group consisting of (C1-C60)alkyl, (C6-C60)aryl, and halogen; R ₈₀ and R ₈₁ independently represent hydrogen, with or without a halogen substituent ( C1-C60)alkyl, or (C6-C60)aryl having or without (C1-C60)alkyl substituent; R ₈₅ independently representing hydrogen, straight or branched chain (C1-C60) alkane a (C6-C60) aryl or a halogen; and the alkyl or aryl group of R ₈₅ may be further substituted with one or more substituents selected from the group consisting of straight or branched with or without a halogen substituent Branch (C1-C60) alkyl, (C1-C30) alkoxy, halogen, tri(C1-C30)alkyldecyl, tris(C6-C30)aryldecyl and (C6-C60)aryl ; R ₈₆ Shows (C1-C60) alkyl, (C6-C60) aryl or halogen; and R86 of the alkyl or aryl groups may be further substituted by halogen or (C1-C60) alkyl group; R ₉₁ to R ₉₈ independently based Ground hydrogen or a straight or branched chain (C1-C60) alkyl group with or without a halogen substituent, (C1-C30) alkoxy group, halogen, tri(C1-C30)alkyl fluorenyl group, three ( C6-C30) arylalkylalkyl or (C6-C60)aryl; and R ₁₀₁ to R ₁₀₈ , R ₁₁₁ and R ₁₁₂ independently represent hydrogen (C1-C60)alkyl with or without a halogen substituent (C1-C30) alkoxy, halogen, (C6-C60) aryl, cyano or (C5-C60)cycloalkyl.

The dopant compound represented by the chemical formula (2) can be exemplified by a compound represented by one of the following structural formulae, but is not limited thereto.

The organic electroluminescent device of the present invention may further comprise, in addition to the organic electroluminescent compound represented by the chemical formula (1), one or more compounds selected from the group consisting of arylamine compounds and styryl arylamine compounds. Examples of the arylamine compound or the styrylarylamine compound include, but are not limited to, the compound represented by the chemical formula (3):

Chemical formula (3)

Wherein, Ar ₁₁ and Ar ₁₂ independently represent (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, (C6-C60)arylamine, (C1-C60) An alkylamino group, a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, or a (C3-C60) cycloalkyl group, or Ar ₁₁ and Ar ₁₂ may be via (C3-C60)alkylene or (C3-C60)alkylene linkage with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when b is 1, Ar ₁₃ Represents (C6-C60) aryl, (C4-C60)heteroaryl, or a substituent represented by one of the following structural formulae:

When b is 2, Ar ₁₃ represents a (C6-C60) extended aryl group, a (C4-C60) heteroaryl group, or a substituent represented by one of the following structural formulas:

Wherein, Ar ₁₄ and Ar ₁₅ independently represent (C6-C60) an extended aryl group or a (C4-C60) heteroaryl group; and R ₂₀₁ to R ₂₀₃ independently represent a hydrogen, hydrazine, (C1-C60) alkyl group. Or (C6-C60) aryl; c is an integer from 1 to 4, d is an integer of 0 or 1; and the alkyl, aryl, heteroaryl, arylamino, alkylamine of Ar ₁₁ and Ar ₁₂ group, a cycloalkyl group or a heterocycloalkyl group, an aryl group or the Ar _13, the aryl, heteroaryl, arylene group or heteroaryl group extends, an arylene group or the Ar ₁₄ and Ar _15, or the extension heteroaryl, or The alkyl or aryl group of R ₂₀₁ to R ₂₀₃ may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60) alkyl, (C6-C60) aryl a (C4-C60)heteroaryl group, a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, tri (C1- C60) alkyl nonylalkyl, di(C1-C60)alkyl (C6-C60) aryldecylalkyl, tris(C6-C60)aryldecylalkyl, adamantyl, (C7-C60)bicycloalkyl, C2-C60) alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl (C1-C60) Alkyl, (C6-C60) aryloxy, (C1-C6 0) alkoxy, (C6-C60) arylthio, (C1-C60)alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)aryl Carbonyl, carboxyl, nitro and hydroxyl groups.

The arylamine compound and the styrylarylamine compound can be more specifically illustrated by the following compounds, but are not limited thereto.

In the organic electroluminescent device of the present invention, the organic layer may include, in addition to the organic electroluminescent compound represented by the chemical formula (1), one or more metals selected from the group consisting of: Group 1 An organometallic, a Group 2 organometallic, a transition metal of the fourth and fifth cycles, a lanthanide metal, and a d-transition element. The organic layer may include both an electroluminescent layer and a charge generating layer.

The present invention can realize an electroluminescent device having a pixel structure of an independent light-emitting mode, including a compound represented by the chemical formula (1) as a sub-pixel, and including one or more components selected from the group consisting of Ir, Pt, Pd, and Rh An organic electroluminescent device in which sub-pixels of one or more metal compounds of the group consisting of Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag are simultaneously patterned in parallel.

Further, an organic display may be formed which, in addition to the organic electroluminescent compound described above, includes one or more compounds selected from the group consisting of compounds having an electroluminescent peak having a wavelength of not more than 560 nm. The compounds having a wavelength of the electroluminescence peak of not more than 560 nm are exemplified by the compounds represented by one of Chemical Formulas (4) to (9), but are not limited thereto.

Chemical formula (4)

In the chemical formula (4), Ar ₂₁ and Ar ₂₂ independently represent (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, (C6-C60)arylamine. (C1-C60)alkylamino group, 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, or (C3-C60)cycloalkyl, or Ar ₂₁ And Ar ₂₂ may be bonded via an (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when e is At 1 o'clock, Ar ₂₃ represents a (C6-C60) aryl group, a (C4-C60)heteroaryl group, or a substituent represented by one of the following structural formulas:

When e is 2, Ar ₂₃ represents a (C6-C60) extended aryl group, a (C4-C60) heteroaryl group, or a substituent represented by one of the following structural formulas:

Wherein, Ar ₂₄ and Ar ₂₅ independently represent (C6-C60) aryl or (C4-C60) heteroaryl; and R ₂₁₁ to R ₂₁₃ independently represent hydrogen, hydrazine, (C1-C60) alkyl Or (C6-C60) aryl; f is an integer from 1 to 4, g is an integer of 0 or 1; and the alkyl, aryl, heteroaryl, arylamine, alkylamine of Ar ₂₁ and Ar ₂₂ a cyclyl or cycloheteroalkyl group, or an aryl, heteroaryl, aryl or heteroaryl group of Ar ₂₃ , or an aryl or heteroaryl group of Ar ₂₄ and Ar ₂₅ , or The alkyl or aryl group of R ₂₁₁ to R ₂₁₃ may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60) alkyl, (C6-C60) aryl a (C4-C60)heteroaryl group, a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, tri (C1- C60) alkyl nonylalkyl, di(C1-C60)alkyl (C6-C60) aryldecylalkyl, tris(C6-C60)aryldecylalkyl, adamantyl, (C7-C60)bicycloalkyl, C2-C60) alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl (C1-C60) Alkyl, (C6-C60) aryloxy, (C1-C6 0) alkoxy, (C6-C60) arylthio, (C1-C60)alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)aryl Carbonyl, carboxyl, nitro and hydroxyl groups.

Chemical formula (5)

In the chemical formula (5), R ₃₀₁ to R ₃₀₄ independently represent hydrogen, hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, containing one or a plurality of 5-membered or 6-membered heterocycloalkyl groups selected from heteroatoms of N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, di(C1-C60)alkane (C6-C60) arylalkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl (C1-C60) alkoxy group, cyano group, (C1-C60)alkylamino group, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C6 -C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxy, nitro or hydroxy, or R ₃₀₁ to R ₃₀₄ may or may not have a fused ring (C3-C60) alkylene or (C3-C60)alkylene group bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; R ₃₀₁ to R ₃₀₄ of the alkyl group, alkene a base, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an arylalkylalkyl group, an alkylalkyl group, an alkylamino group or an arylamino group, or a R ₃₀₁ to R _{304 group} having Or without a fused ring (C3-C60) alkylene (C3-C60) an alicyclic ring formed by an alkenyl group bonded to an adjacent substituent, or a monocyclic or polycyclic aromatic ring, may be further substituted with one or more substituents selected from the group consisting of hydrazine, Halogen, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, 5- or 6-membered heterocyclic ring containing one or more heteroatoms selected from N, 0 and S Alkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl,tri(C6-C60)aryldecane Alkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C1-C60)alkoxy, cyano, (C1-C60)alkyl Amine, (C6-C60) arylamine, (C6-C60) aryl (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60 An alkoxycarbonyl group, a carboxyl group, a nitro group, and a hydroxyl group.

Chemical formula (6)

Chemical formula (7)

Chemical formula (8)

In the chemical formulae (6) to (8), R ₃₂₁ and R ₃₂₂ independently represent (C6-C60) aryl, (C4-C60)heteroaryl, or one or more selected from N, O and S. a 5- or 6-membered heterocycloalkyl or a (C3-C60)cycloalkyl group of a hetero atom, and the aryl or heteroaryl group of R ₃₂₁ and R ₃₂₂ may be further composed of one or more selected from the group consisting of Substituted by a group of substituents: anthracene, (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, (C6-C60) Aryl, (C4-C60)heteroaryl, halogen, cyano, tri(C1-C60)alkyldecyl, bis(C1-C60)alkyl(C6-C60)aryldecyl and tris(C6- C60) aryl decyl group; R ₃₂₃ to R ₃₂₆ independently represent hydrogen, hydrazine, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5 a -C60)cycloalkyl or (C6-C60)aryl group, and the heteroaryl, cycloalkyl or aryl group of R ₃₂₃ to R ₃₂₆ may further be substituted with one or more substituents selected from the group consisting of Substituted: fluorene, (C1-C60)alkyl, (C1-C60) alkoxy, (C3-C60)cycloalkyl, halogen, cyano, tri(C1-C60) with or without a halogen substituent Alkylalkyl, di(C1-C60) alkane a (C6-C60) arylalkylalkyl group and a tri(C6-C60)aryldecylalkyl group; the G ₁ and G ₂ systems independently represent a chemical bond or have one or more substituents selected from the group consisting of C6-C60) aryl group: (C1-C60) alkyl group, (C1-C60) alkoxy group, (C6-C60) aryl group, (C4-C60) heteroaryl group and halogen; Ar ₃₁ and Ar ₃₂ series Represents a (C4-C60)heteroaryl or aryl group selected from the following structures:

The aryl or heteroaryl group of Ar ₃₁ and Ar ₃₂ may be further substituted with one or more substituents selected from the group consisting of hydrazine, (C1-C60) alkyl, (C1-C60) alkoxy, (C6) -C60) aryl and (C4-C60)heteroaryl; L ₁₁ represents (C6-C60) extended aryl, (C4-C60) heteroaryl or a compound represented by the following structure:

The aryl or heteroaryl group of L ₁₁ may be substituted with one or more substituents selected from the group consisting of hydrazine, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60). Aryl, (C4-C60)heteroaryl and halogen; R ₃₃₁ to R ₃₃₄ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl or (C6-C60)aryl; or R ₃₃₁ to R ₃₃₄ may be bonded to an adjacent substituent via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic moiety. Rings; R ₃₄₁ to R ₃₄₄ are independently represented by hydrogen, hydrazine, (C1-C60)alkyl, (C1-C60)alkoxy, (C6-C60)aryl, (C4-C60)heteroaryl or halogen. Or R ₃₄₁ to R ₃₄₄ may be bonded to an adjacent substituent via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a single ring; Or a multi-ring aromatic ring.

Chemical formula (9)

In the chemical formula (9), L ₂₁ represents a (C6-C60) extended aryl group, a (C3-C60) heteroaryl group containing one or more hetero atoms selected from N, O and S or selected from the following structures. Divalent group:

L ₂₂ and L ₂₃ independently represent a chemical bond, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60) extended aryloxy, (C6-C60) An arylthio group, a (C6-C60) extended aryl group, or a (C3-C60) heteroaryl group containing one or more hetero atoms selected from N, O and S; and Ar ₄₁ represents NR ₄₂₃ R ₄₂₄ , C6-C60) aryl, (C3-C60)heteroaryl containing one or more heteroatoms selected from N, O and S, 5 members containing one or more heteroatoms selected from N, O and S Or 6 membered heterocycloalkyl, (C3-C60)cycloalkyl, adamantyl, (C7-C60)bicycloalkyl, or a substituent selected from the group consisting of:

Wherein R ₄₀₁ to R ₄₁₁ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, or one or more heteroatoms selected from N, O and S ( C3-C60) Heteroaryl, N-morpholinyl, thio-N-morpholinyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O and S, (C3 -C60) cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl,tri(C6-C60)aryldecyl,adamantyl (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamine, C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carboxy, nitro or hydroxy, or R ₄₀₁ to R ₄₁₁ , respectively, with or without condensing rings (C3-C60) alkylene or (C3-C60) alkenylene group bonded to an adjacent substituent group to form an alicyclic ring, or a monocyclic aromatic ring or rings; R412 to R ₄₂₂ independently represent hydrogen based , hydrazine, halogen, (C1-C60) alkyl, (C6-C60) aryl, containing (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, having one or more heteroatoms selected from N, O and S, containing one or more selected from N, O and S 5- or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecane , tris(C6-C60)arylalkylalkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60) Alkylamino group, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C1-C60) alkoxy group, (C1-C60) alkylthio group, (C6 -C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy Or R ₄₁₂ to R ₄₂₂ may be bonded to an adjacent substituent via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a single ring Or a polycyclic aromatic ring; R ₄₂₃ and R ₄₂₄ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, containing one or more selected from N, O and S Heteroatom (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, di(C1) -C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2- C60) alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6 -C60) an arylcarbonyl group, a carboxyl group, a nitro group or a hydroxyl group, or R ₄₂₃ and R ₄₂₄ may be bonded via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring. Forming an alicyclic ring, or a monocyclic or polycyclic aromatic ring; R ₄₂₅ to R ₄₃₆ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, containing one or more (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, hetero atom containing N, O and S, containing one or more heteroatoms selected from N, O and S 5- or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkylhydrazine , bis(C1-C60)alkyl (C6-C60) aryl decyl, tris(C6-C60) arylalkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) olefin , (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C1 -C60) alkoxy group, (C1-C60)alkylthio group, (C6-C60) aryloxy group, (C6-C60) arylthio group, (C1-C60) alkoxycarbonyl group, (C1-C60) alkane Alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or R ₄₂₅ to R ₄₃₆ may be via (C3-C60)alkyl or (C3-C60), respectively, with or without a fused ring. An alkenyl group is bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; E and F independently represent a chemical bond, -(CR ₄₃₇ R ₄₃₈ ) _i -, -N(R ₄₃₉ ) -, -S-, -O-, -Si(R ₄₄₀ )(R ₄₄₁ )-, -P(R ₄₄₂ )-, -C(=O)-, -B(R ₄₄₃ )-, -In(R ₄₄₄ )-, -Se-, -Ge(R ₄₄₅ )(R ₄₄₆ )-, -Sn(R ₄₄₇ )(R ₄₄₈ )-, -Ga(R ₄₄₉ )- or -(R ₄₅₀ )C=C(R ₄₅₁ )-; R ₄₃₇ to R ₄₅₁ independently represent hydrogen, hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, containing one or more heteroatoms selected from N, O and S. (C3-C60)heteroaryl N-morpholinyl, thio N-morpholinyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, three (C1-C60) alkyl nonyl, di(C1-C60)alkyl(C6-C60)aryldecyl, tris(C6-C60)aryldecyl,adamantyl,(C7-C60)bicycloalkane , (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl (C1 -C60)alkyl, (C1-C60)alkoxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxy Carbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carboxy, nitro or hydroxy, or R437 and R ₄₃₈ , R ₄₄₀ and R ₄₄₁ , R ₄₄₅ and R ₄₄₆ , R ₄₄₇ and R ₄₄₈ And R ₄₅₀ and R ₄₅₁ may be bonded via an (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring. The aryl or heteroaryl group of L ₂₁ to L ₂₃ , the aryl or heteroaryl group of Ar ₄₁ , or R ₄₀₁ to R ₄₁₁ , R ₄₁₂ to R ₄₂₂ , R ₄₂₃ , R ₄₂₄ , R ₄₂₅ to R _436, and R ₄₃₇ to R ₄₅₁ of the alkyl group, aryl group, heteroaryl group Heterocycloalkyl, cycloalkyl, trialkylalkyl, dialkylarylalkyl, triarylalkyl, alkenyl, alkynyl, alkylamino or arylamine groups, further independently Or a plurality of substituents selected from the group consisting of hydrazine, halogen, (C1-C60)alkyl, halo(C1-C60)alkyl, (C6-C60)aryl, containing one or more selected from N, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl having 0 or S heteroatoms and having or without (C6-C60) aryl substituents, containing one or more 5- or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl (C6) heteroatoms of N, O and S -C60) arylalkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano (C1-C60)alkylamino group, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C1-C60) alkoxy group, (C1-C60) Alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, Carboxyl, nitro, hydroxyl,

h is an integer from 1 to 4; and i is an integer from 1 to 4.

The compounds having a wavelength of the electroluminescence peak of not more than 560 nm can be specifically exemplified by the following compounds, but are not limited thereto.

In the organic electroluminescence device of the present invention, one or more layers (hereinafter referred to as "surface layer") are preferably selected from the group consisting of a chalcogenide layer, a metal halide layer and a metal oxide layer. The layer body is disposed on an inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to provide a chalcogen compound layer of bismuth and aluminum metal (including an oxide) on the anode surface of the EL medium layer, and to provide a metal halide layer or a metal oxide layer on the anode layer. On the cathode surface of the EL dielectric layer. Thereby, operational stability can be obtained.

Examples of the chalcogen compound preferably include SiO _X (1≦X≦2), AlO _X (1≦X≦1.5), SiON, SiAlON, and the like. Examples of the metal halide preferably include LiF, MgF ₂ , CaF ₂ , a fluoride of a rare earth metal, and the like. Examples of the metal oxide preferably include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In the organic electroluminescent device of the present invention, it is also preferred to provide a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant in the above-mentioned manufacturing. On at least one surface of the pair of electrodes. Thereby, the electron transporting compound is reduced to an anion, thereby causing electrons to be injected from the mixed region and transported to the EL medium. In addition, since the hole transporting compound is oxidized to form a cation, the hole is caused to be injected from the mixed region and transported to the EL medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof.

The electroluminescent device of the present invention exhibits excellent luminous efficiency, good color purity, and excellent operational life using lower operating voltages.

[Best mode]

The invention is further described by reference to the preparation examples and the examples for illustrating the luminescent properties of the novel electroluminescent device of the invention, but the examples provided are merely for facilitating an understanding of the invention and are not intended to be in any form. Limit the scope of the invention.

Preparation example

Preparation Examples 1 to 18 are described in Korean Patent Registration No. 0684109.

[Preparation Example 1] Preparation of Compound (1)

2-pyridin-2-yl-phenol (1.0 g (g), 5.84 mmol (mmol)) was dissolved in methanol (50 ml (mL)), and 1 mol concentration (M) aqueous sodium hydroxide solution was added. (10 mL). To the mixture was added a solution of sulphuric acid sulphate tetrahydrate (1.05 g, 5.93 mmol) in methanol (methanol 7 mL: water, 3 mL), and the mixture was stirred at ambient temperature for 2 hr. Then, the addition of 2-hydroxy-phenylbenzene is slowly added. Azole (1.54 g, 7.30 mmol) in methanol (50 mL). The reaction mixture was stirred at ambient temperature for a further 2 hours and heated to 50 °C. After stirring for 10 hours, the resulting residue was filtered, washed with w~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

MS/FAB: 391 (measured value); 391.43 (calculated value)

EA: C73.55%, H 4.59%, N 7.05%, 010.41%

[Preparation Example 2] Preparation of Compound (2)

2-Pyridin-2-yl-phenol (1.0 g, 5.84 mmol) was dissolved in methanol (50 mL) and 1M aqueous sodium hydroxide (10 mL). A solution of zinc acetate (0.95 g, 5.18 mmol) in methanol (10 mL of methanol) was added dropwise to this mixture, and the mixture was stirred at ambient temperature for 2 hr. Then, the addition of 2-hydroxy-phenylbenzene is slowly added. Azole (1.50 g, 7.10 mmol) in methanol (50 mL). The reaction mixture was stirred for a further 10 hours at ambient temperature. The resulting precipitate was filtered, washed with water (50 mL)

MS/FAB: 447 (measured value); 447.79 (calculated value)

EA: C 64.22%, H 4.01%, N 6.05%, 0 10.95%

[Preparation Example 3] Preparation of Compound (3)

Using 2-hydroxy-phenyl benzo The same procedure as described in Preparation Example 1 was repeated, azole (1.23 g, 5.82 mmol), 10-hydroxybenzo[h]quinoline (1.48 g, 7.58 mmol) and barium sulfate tetrahydrate (1.05 g, 5.93 mmol). The title compound, compound (3) (0.35 g, 0.84 mmol, yield: 14%) was obtained.

MS/FAB: 415 (measured value); 415.46 (calculated value)

EA: C 75.02%, H 4.27%, N 6.64%, 0 11.65%

[Preparation Example 4] Preparation of Compound (4)

Using 2-hydroxy-phenyl benzo The title compound was obtained by repeating the same procedure as described in Preparation 2, azole (1.23 g, 5.82 mmol), 10-hydroxybenzo[h]quinoline (1.48 g, 7.58 mmol) and zinc acetate (0.95 g, 5.18 mmol). Compound (4) (0.52 g, 1.10 mmol, yield: 19%).

MS/FAB: 471 (measured value); 471.81 (calculated value)

EA: C 66.08%, H 3.79%, N 5.84%, O 10.30%

[Preparation Example 5] Preparation of Compound (5)

Using 2-hydroxy-phenyl benzo The same procedure as described in Preparation Example 1 was repeated, azole (1.23 g, 5.82 mmol), 2-hydroxy-phenylbenzothiazole (1.72 g, 7.57 mmol), and ruthenium sulfate tetrahydrate (1.05 g, 5.93 mmol). The title compound, compound (5) (0.96 g, 2.15 mmol, yield: 37%).

MS/FAB: 447 (measured value); 447.52 (calculated value)

EA: C69.68%, H 4.01%, N 6.16%, O 10.85%, S 7.05%

[Preparation Example 6] Preparation of Compound (6)

Using 2-hydroxy-phenyl benzo The title compound was obtained by repeating the same procedure as described in Preparation 2, EtOAc (EtOAc, EtOAc, EtOAc, EtOAc Compound (6) (1.36 g, 2.70 mmol, yield: 46%).

MS/FAB: 503 (measured value); 503.88 (calculated value)

EA: C 61.88%, H 3.54%, N 5.46%, O 9.73%, S 6.26%

[Preparation Example 7] Preparation of Compound (7)

Repeated preparation using 2-hydroxy-phenylbenzothiazole (1.32 g, 5.80 mmol), 2-pyridin-2-yl-phenol (1.30 g, 7.59 mmol) and barium sulfate tetrahydrate (1.05 g, 5.93 mmol). The title compound, Compound (7) (0.59 g, 1.45 mmol, yield: 25%).

MS/FAB: 407 (measured value); 407.50 (calculated value)

EA: C 70.64%, H 4.35%, N 6.76%, 0 7.96%, S 7.75%

[Preparation Example 8] Preparation of Compound (8)

Preparation Example 2 was repeated using 2-hydroxy-phenylbenzothiazole (1.32 g, 5.80 mmol), 2-pyridin-2-yl-phenol (1.30 g, 7.59 mmol), and zinc acetate (0.95 g, 5.18 mmol). The title compound, Compound (8) (0.83 g, 1.79 mmol, yield: 31%) was obtained.

MS/FAB: 463 (measured value); 463.86 (calculated value)

EA: C62.04%, H3.82%, N5.98%, 07.02%, S6.83%

[Preparation Example 9] Preparation of Compound (9)

2-Hydroxy-phenylbenzothiazole (1.32 g, 5.80 mmol), 10-hydroxybenzo[h]quinoline (1.48 g, 7.58 mmol) was used to replace 2-hydroxy-phenylbenzo The title compound, Compound (9) (0.98 g, 2.27 mmol, yield: 39%) was obtained from the title compound.

MS/FAB: 431 (measured value); 431.52 (calculated value)

EA: C72.22%, H4.10%, N6.40%, 07.62%, S7.33%

[Preparation Example 10] Preparation of Compound (10)

Preparation Example 4 was repeated using 2-hydroxy-phenylbenzothiazole (1.32 g, 5.80 mmol), 10-hydroxybenzo[h]quinoline (1.48 g, 7.58 mmol), and zinc acetate (0.95 g, 5.18 mmol). The same procedure as described above gave the title compound, Compound (10) (1.22 g, 2.50 mmol, yield: 43%).

MS/FAB: 487 (measured value); 487.88 (calculated value)

EA: C 63.93%, H 3.65%, N 5.64%, O 6.70%, S 6.44%

[Preparation Example 11] Preparation of Compound (11)

Using 2-hydroxy-phenyl benzo Azole (1.23 g, 5.82 mmol), 2-(1-phenyl-1H-benzimidazol-2-yl)-phenol (2.17 g, 7.58 mmol) and cesium sulfate tetrahydrate (1.05 g, 5.93 mmol). The same procedure as described in Preparation 1 was repeated to give the title compound, Compound (11) (0.56 g, 1.11 mmol, yield: 19%).

MS/FAB: 506 (measured value); 506.57 (calculated value)

EA: C 75.67%, H 4.50%, N 8.20%, O 9.68%

[Preparation Example 12] Preparation of Compound (12)

Using 2-hydroxy-phenyl benzo Preparation of azole (1.23 g, 5.82 mmol), 2-(1-phenyl-1H-benzimidazol-2-yl)-phenol (2.17 g, 7.58 mmol) and zinc acetate (0.95 g, 5.18 mmol) The title compound (12) (0.72 g, 1.28 mmol, yield: 22%).

MS/FAB: 562 (measured value); 562.93 (calculated value)

EA: C68.16%, H4.05%, N7.36%, 08.68%

[Preparation Example 13] Preparation of Compound (13)

2-(1-Phenyl-1H-benzimidazol-2-yl)-phenol (1.67 g, 5.83 mmol), 2-pyridin-2-yl-phenol (1.30 g, 7.59 mmol) and barium sulfate tetrahydrate The title compound (13) (0.84 g, 1.80 mmol, yield: 31%) was obtained.

MS/FAB: 466 (measured value); 466.55 (calculated value)

EA: C77.08%, H4.87%, N8.90%, 06.98%

[Preparation Example 14] Preparation of Compound (14)

2-(1-Phenyl-1H-benzimidazol-2-yl)-phenol (1.67 g, 5.83 mmol), 2-pyridin-2-yl-phenol (1.30 g, 7.59 mmol) and zinc acetate (0.95) were used. The same procedure as described in Preparation 2 was repeated to give the title compound, Compound (14) (0.88 g, 1.68 mmol, yield: 29%).

MS/FAB: 522 (measured value); 522.91 (calculated value)

EA: C 68.81%, H 4.33%, N 7.92%, O 6.32%

[Preparation Example 15] Preparation of Compound (15)

2-(1-Phenyl-1H-benzimidazol-2-yl)-phenol (1.67 g, 5.83 mmol), 10-hydroxybenzo[h]quinoline (1.50 g, 7.68 mmol) and barium sulfate The title compound (15) (0.53 g, yield: 9%) was obtained.

MS/FAB: 490 (measured value); 490.57 (calculated value)

EA: C 78.20%, H 4.68%, N 8.42%, O 6.70%

[Preparation Example 16] Preparation of Compound (16)

2-(1-Phenyl-1H-benzimidazol-2-yl)-phenol (1.67 g, 5.83 mmol), 10-hydroxybenzo[h]quinoline (1.50 g, 7.68 mmol) and zinc acetate ( The title compound (16) (0.42 g, 0.77 mmol, yield: 13%) was obtained.

MS/FAB: 546 (measured value); 546.93 (calculated value)

EA: C 70.13%, H 4.16%, N 7.58%, O 5.98%

[Preparation Example 17] Preparation of Compound (17)

2-Hydroxy-phenylbenzothiazole (1.32 g, 5.80 mmol), 2-(1-phenyl-1H-benzimidazol-2-yl)-phenol (2.17 g, 7.58 mmol) and barium sulfate tetrahydrate The title compound (17) (0.64 g, 1.22 mmol, yield: 21%) was obtained.

MS/FAB: 522 (measured value); 522.64 (calculated value)

EA: C 73.42%, H 4.34%, N 7.97%, O 6.25%, S 6.04%

[Preparation Example 18] Preparation of Compound (18)

2-Hydroxy-phenylbenzothiazole (1.32 g, 5.80 mmol), 2-(1-phenyl-1H-benzimidazol-2-yl)-phenol (2.17 g, 7,58 mmol) and zinc acetate ( The title compound (18) (0.94 g, 1.62 mmol, yield: 28%) was obtained.

MS/FAB: 578 (measured value); 578.99 (calculated value)

EA: C 66.22%, H 3.94%, N 7.16%, O 5.70%, S 5.49%

[Preparation Example 19] Preparation of Compound (19)

Preparation of Compound (A)

5-Bromo-2-hydroxybenzaldehyde (20.0 g, 99.5 mmol), phenylboronic acid (13.4 g, 109.5 mmol) and hydrazine (triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) (5.8 g) , 5.0 mmol) was dissolved in 2,3-butanediol (200 mL) and ethanol (100 mL). A 2 M aqueous potassium carbonate solution (132 mL) was added, and the mixture was stirred at <RTIgt; When the reaction was completed, water (100 mL) was added to the reaction mixture to terminate the reaction. The mixture was extracted with ethyl acetate (200 mL) and dried and evaporated. Purification by column chromatography (n-hexane: MC = 1:5) gave Compound (A) (12.0 g, 61.0 mmol).

Preparation of compound (B)

2-Aminothiophenol (3.8 g, 30.2 mmol) and compound (A) (5.0 g, 25.2 mmol) were dissolved in 1,4-two The mixture was stirred at 100 ° C for 12 hours under aq. (12 mL). When the reaction was completed, the reaction mixture was cooled to room temperature and extracted with dichloromethane (100mL) and water (100mL). The extract was dried under reduced pressure and the residue was purified mjjjjjjjjjjj

Preparation of Compound (19)

Compound (B) (4.5 g, 14.8 mmol) and sodium hydroxide (0.6 g, 14.8 mmol) were dissolved in ethanol (100 mL). After stirring the solution for 30 minutes, Zn(CH ₃ COO) ₂ , 2H ₂ O (1.8 g, 8.2 mmol) was slowly added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was washed with EtOAc EtOAc (EtOAc) . [Preparation Example 20] Preparation of Compound (178)

Preparation of compound (C)

5-Iodoporphyrin-2,3-dione (10.0 g, 36.6 mmol) and phenylboronic acid (5.4 g, 43.9 mmol) were dissolved in 2,3-butanediol (600 mL). To the solution were added hydrazine (triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) (2.1 g, 1.8 mmol) and 2M aqueous sodium hydrogencarbonate (120 mL). The mixture was stirred at reflux for 12 hours and the solvent was removed upon completion of the reaction. A 5% aqueous sodium hydroxide solution (120 mL) was added to the residue, and the mixture was stirred at room temperature. The aqueous solution was extracted with dichloromethane and the aqueous layer was collected. After adding a 30% aqueous hydrogen peroxide solution (120 mL), the temperature was raised to 50 ° C and stirred for 30 minutes. After cooling to room temperature, a 1 N aqueous hydrochloric acid solution was slowly added to the aqueous solution to adjust the pH to 4. The resulting solid was filtered and dried under reduced pressure to give compound (c) (5.5 g, 26.0 mmol).

Preparation of Compound (D)

Compound (C) (7.1 g, 33.3 mmol) was dissolved in water (18 mL) and concentrated hydrochloric acid (7 mL). After 10 minutes, the temperature was lowered to 0 ° C, and sodium nitrate (NaN0 ₃ ) (2.3 g, 33.3 mmol) dissolved in water (10 mL) was slowly added. Then, the temperature was maintained at 0 ° C while stirring the resulting mixture. In a separate reaction vessel, sodium sulfide nonahydrate (Na ₂ S‧9H ₂ O) (9.6 g, 39.9 mmol) and sulfur (1.3 g, 39.9 mmol) were dissolved in water (10 mL) and 10 M hydrogen was added. An aqueous solution of sodium oxide (4 mL). This mixture was added to the reaction mixture at 0 ° C, and the resulting mixture was heated to room temperature and stirred until no more gas was produced. When the reaction was completed, concentrated hydrochloric acid was added until a solid was produced, then the mixture was filtered under reduced pressure. The resulting solid was added to sodium bicarbonate (NaHCO ₃₎ solution (85 mL), and the mixture was stirred at reflux for 20 minutes and cooled to room temperature. After removing the undissolved solid (impurities), concentrated hydrochloric acid was added to the aqueous solution to again produce a solid. The solid obtained by filtration under reduced pressure was added to ethanol (30 mL), and the mixture was stirred under reflux for 20 min. Undissolved solids (impurities) were removed and the filtrate was concentrated. Zinc (2.2 g, 33.3 mmol) and glacial acetic acid (30 mL) were added and the mixture was stirred at reflux for 48 hr. When the reaction was completed, the reaction mixture was cooled to room temperature, and the collected solid was added to a 5M aqueous sodium hydroxide solution (63 mL), and the mixture was stirred under reflux for 30 minutes. After the undissolved solids (impurities) were removed, concentrated hydrochloric acid was added in small portions to acidify the aqueous solution. Next, the resulting solid was collected and added to ethanol (20 mL). After stirring under reflux for 30 minutes, the undissolved solid (impurity) was removed, and the filtrate was concentrated to give Compound (D) (1.8 g, 7.6 mmol).

Preparation of compound (E)

In a reaction vessel, Compound (D) (5.0 g, 21.7 mmol), 2-aminothiophenol (2.1 mL, 19.5 mmol) and polyphosphoric acid (20 g) were stirred under reflux at 140 ° C for 24 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and the pH was adjusted to neutral by slowly adding a saturated aqueous solution of sodium hydroxide. The resulting solid was then filtered under reduced pressure to give a solid product. The solid was washed with ethanol and dried to give Compound (E) (5.4 g, 17.1 mmol).

Preparation of Compounds (178)

Compound (E) (5.0 g, 15.6 mmol) and sodium hydroxide (0.6 g, 15.6 mmol) were dissolved in ethanol (100 mL) and the solution was stirred for 30 min. After Zn(CH ₃ COO) ₂ ‧2H ₂ O (1.9 g, 8.7 mmol) was slowly added, the mixture was stirred at room temperature for 12 hours. The mixture was washed with EtOAc (EtOAc) (EtOAc)

Compounds 19 to 336 listed in Table 1 were prepared according to the same procedures as Preparations 19 and 20, and the ¹ H NMR and MS/FAB data of the compounds are shown in Table 2. The compounds listed in Table 1 are compounds containing a divalent metal M.

[Preparation Example 21] Preparation of Compound (337)

Compound (B) (4.5 g, 14.8 mmol) and aluminum isopropoxide (3.0 g, 14.8 mmol) were dissolved in chloroform (50 mL) / isopropyl alcohol (150 mL), and the mixture was stirred at 60 ° C for 3 hours. When the solution became clear, 4-phenylphenol (3.0 g, 17.8 mmol) was added, and the mixture was stirred under reflux at 80 ° C for 3 hours. Then, the compound (B) (4.5 g, 14.8 mmol) was further added, and the mixture was stirred under reflux for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The solid was washed with EtOAc (EtOAc) (EtOAc)

Compounds 337 to 426 listed in Table 3 were prepared according to the same procedure as in Preparation 21, and the ¹ H NMR and MS/FAB data of the compounds are listed in Table 4. The compounds listed in Table 3 are compounds containing a trivalent metal M.

[Example 1] Production of OLED

An OLED device is fabricated using the red phosphorescent compound of the present invention.

First, the transparent electrode (2) ITO film (15 Ω / □) obtained by OLED glass (manufactured by Samsung Corning) (1) was washed with trichloroethylene, acetone, ethanol, and distilled water in sequence, and stored. Used in isopropanol.

Then, the ITO substrate was assembled in a substrate holder of a vacuum vapor deposition apparatus, and 4,4',4"-parameter (N,N-(2-naphthyl)-phenylamino)triphenylamine ( 2-TNATA) is placed in a cell of the vacuum vapor deposition apparatus, which is then vented in the chamber to achieve a vacuum of 10 ^-6 torr. A current is applied to the chamber to evaporate 2-TNATA, thereby A hole injection layer (3) having a thickness of 60 nm (nm) was vapor-deposited on the ITO substrate.

Next, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is loaded into another chamber of the vacuum vapor deposition apparatus, The chamber applies a current to evaporate the NPB, thereby vapor-depositing a hole transport layer (4) having a thickness of 20 nm on the hole injection layer.

The electroluminescence host material (H-26) of the present invention is filled in another chamber of the vacuum vapor deposition apparatus, and the red phosphorescent compound (compound D-4) of the present invention is filled in a further chamber. The two materials are evaporated at different rates for doping, whereby an electroluminescent layer (5) having a thickness of 30 nm is vapor-deposited on the hole transport layer. Preferably, the doping concentration is from 4 to 10% by weight based on the host material.

Next, a 20 nm thick octagonal (8-hydroxyquinoline) aluminum (III) (Alq) (tris (8-hydroxyquinoline) aluminum (III)) was deposited as an electron transport layer (6), and the vapor deposition thickness was 1 to 2 nm of lithium quinolate (Liq) was used as the electron injecting layer (7). Thereafter, an aluminum (Al) cathode (8) having a thickness of 150 nm was vapor-deposited by using another vacuum vapor deposition apparatus to fabricate an OLED.

[Comparative Example 1] Manufacture of OLED using a conventional phosphorescent material

After the hole injection layer and the hole transport layer were formed in accordance with the same procedure as in Example 1, the electroluminescent layer was vapor-deposited in the following manner.

The other chamber of the vacuum vapor deposition apparatus is filled with 4,4'-N,N'-dicarbazole-biphenyl (CBP) as an electroluminescent host material, and the red color of the present invention is filled in another chamber. Phosphorescent compound (Compound D-4). The two materials are evaporated at different rates for doping, whereby an electroluminescent layer (5) having a thickness of 30 nm is vapor-deposited on the hole transport layer. A preferred doping concentration is from 4 to 10% by weight based on CBP.

Next, bis(2-methyl-8-hydroxyquinoline)(p-phenylphenol)aluminum(III)(BAlq)(bis(2-) is vapor deposited on the electroluminescent layer according to the same procedure as the deposition of NPB. Methyl-8-quinolinato)(p-phenylphenolato)aluminum(III)) as a hole barrier layer, followed by vapor deposition of ginseng (8-hydroxyquinoline) aluminum (III) (Alq) having a thickness of 20 nm as an electron transport layer (6). Thereafter, lithium quinolate (Liq) having a thickness of 1 to 2 nm is vapor-deposited as an electron injection layer (7), and an aluminum cathode (8) having a thickness of 150 nm is vapor-deposited by using another vacuum vapor deposition apparatus. To manufacture OLEDs.

[Test Example 1] Evaluation of the performance of the manufactured OLED device

In order to examine the performance of the OLED, the OLED of Example 1 comprising the electroluminescent compound of the present invention was measured at 10 mA/cm 2 (mA/cm ² ), and the conventional electroluminescent compound produced in Comparative Example 1 was included. The luminous efficiency of both OLEDs, and the results are shown in Table 5.

By using the host material of the present invention and a dopant, a red phosphorescent EL device having a high luminous efficiency of a maximum of 12.6 candelas per ampere (cd/A) can be produced. The OLED system fabricated using the host material of the present invention exhibits comparable or higher efficiency than the device fabricated using the conventional phosphorescent EL host material CBP without the use of a hole blocking layer.

The device of the present invention can significantly reduce the power consumption of the OLED by reducing the operating voltage by 0.9 to 1.7 volts V.

If the present invention is applied to mass production of OLEDs, it is also possible to shorten the time required for mass production and greatly contribute to commercialization.

1. . . glass

2. . . Transparent electrode

3. . . Hole injection layer

4. . . Hole transport layer

5. . . Electroluminescent layer

6. . . Electronic transport layer

7. . . Electron injection layer

8. . . Aluminum cathode

Figure 1 is a cross-sectional view of an OLED.

1. . . glass

2. . . Transparent electrode

3. . . Hole injection layer

4. . . Hole transport layer

5. . . Electroluminescent layer

6. . . Electronic transport layer

7. . . Electron injection layer

8. . . Aluminum cathode

Claims (12)

An electroluminescent device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more of 1) a host material compound represented by one or more electroluminescent dopants represented by the chemical formula (2): Chemical formula (1) L ¹ L ² M(Q) _y Chemical formula (2) M ¹ L ³ L ⁴ L ⁵ Wherein the ligands L ¹ and L ² are independently selected from the following structures: Wherein M represents a divalent or trivalent metal; when M is a divalent metal, y is 0; and when M is a trivalent metal, y is 1; Q represents (C6-C60) aryloxy or tri (C6) -C60) arylalkylalkyl, and the aryloxy or triarylsulfanyl group of Q may be further substituted by (C1-C60)alkyl or (C6-C60)aryl; X represents O or S; ring A and Ring B is independently a 5- or 6-membered heteroaryl ring, or a 5- or 6-membered heteroaryl ring fused to a (C6-C60) aromatic ring; Ring A can form a chemical bond with R ₁ to form a fused ring, And Ring A or Ring B may be further substituted with one or more substituents selected from the group consisting of: (C1-C60)alkyl, halogen, halogen-substituted (C1-C60)alkyl, (C6-C60) aryl , (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl , a di(C1-C30)alkylamino group and a di(C6-C30)arylamino group; R ₁ to R ₇ independently represent hydrogen, (C1-C60)alkyl, halogen, having a halogen substituent ( C1-C60) alkyl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl, (C6- C60) aryl, (C4-C60) heteroaryl a bis(C1-C30)alkylamino group and a di(C6-C30)arylamino group; or R ₁ to R ₇ may be bonded to an adjacent substituent via an alkyl or alkenyl group, respectively, to form a thick And aryl or heteroaryl substituted on ring A or ring B, or the aryl or heteroaryl group of R ₁ to R ₇ or R ₁ to R ₇ via alkyl or alkenyl The fused ring bonded to an adjacent substituent may be further substituted with one or more substituents selected from the group consisting of: (C1-C60)alkyl, halogen, cyano, having a halogen substituent ( C1-C60)alkyl, (C3-C60)cycloalkyl, (C1-C30)alkoxy, (C6-C60)aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyl矽alkyl, bis(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl, bis(C1-C30)alkylamino and bis(C6-C30)aryl An amino group; wherein the M ¹ group is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15, and Group 16 of the Periodic Table; The group, and the ligands L ³ , L ⁴ and L ⁵ are independently selected from the following structures: Wherein R ₆₁ to R ₆₃ independently represent a hydrogen (C1-C60) alkyl group having or not having a halogen substituent, and a (C6-C60) aryl group having or not having a (C1-C60) alkyl substituent; Or a halogen; R ₆₄ to R ₇₉ independently represent hydrogen, (C1-C60)alkyl, (C1-C30)alkoxy, (C3-C60)cycloalkyl, (C2-C30)alkenyl, ( C6-C60) aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, SF ₅ , tri(C1-C30)alkyldecyl, di(C1 -C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, cyano or halogen; or R ₇₀ to R ₇₆ may be alkyl (C2-C12) or C2-C12) an alkenyl group bonded to an adjacent substituent to form a fused or polyfused ring; and the alkyl, cycloalkyl, alkenyl or aryl group of R ₆₄ to R ₇₉ , or R ₇₀ and The fused or polycondensed ring formed by R ₇₆ via an alkyl or alkenyl linkage may be further subjected to one or more selected from the group consisting of (C1-C60)alkyl, (C6-C60)aryl, and the halogen substituents; R ₈₀ to R ₈₃ independently represent hydrogen system, with or without halogen substituent group of (C1-C60) alkyl, or with or without (C1-C60) alkyl substituted with The (C6-C60) aryl; R ₈₄ and R ₈₅ independently represent a hydrogen based, linear or branched chain (C1-C60) alkyl, (C6-C60) aryl or halogen; or R ₈₄ and R ₈₅ An alicyclic or monocyclic or polycyclic aromatic ring can be formed via a (C3-C12)alkylene group or a (C3-C12)alkylene group with or without a fused ring; and R ₈₄ and R ₈₅ The alicyclic ring or the monocyclic or polycyclic aromatic ring formed by the alkyl group, the aryl group or the R ₈₄ and R ₈₅ via a (C3-C12)alkylene group or a (C3-C12)alkylene group linkage. Further substituted with one or more substituents selected from the group consisting of a straight or branched chain (C1-C60) alkyl group with or without a halogen substituent, (C1-C30) alkoxy group, halogen, three (C1-C30)alkylalkylalkyl, tris(C6-C30)aryldecylalkyl, and (C6-C60)aryl; R ₈₆ represents (C1-C60)alkyl, (C6-C60)aryl, (C5 -C60)heteroaryl or halogen; R ₈₇ to R ₈₉ independently represent hydrogen, (C1-C60)alkyl, (C6-C60)aryl or halogen, and the alkyl or aryl of R ₈₆ to R ₈₉ The group may be further substituted by halogen or (C1-C60)alkyl; and z represents , or Wherein R ₁₀₁ to R ₁₁₂ independently represent hydrogen, (C1-C60)alkyl group having or without a halogen substituent, (C1-C30) alkoxy group, halogen, (C6-C60) aryl group, cyanide Or a (C5-C60)cycloalkyl group, or R ₁₀₁ to R ₁₁₂ may be bonded to an adjacent substituent via an alkyl or alkenyl group, respectively, to form a (C5-C7) spiro ring or a (C5-C9) thick Ring-bonded, or R ₁₀₁ to R ₁₁₂ may be bonded to R ₆₇ or R ₆₈ via an alkyl or alkenyl group to form a (C5-C7) fused ring. The electroluminescent device of claim 1, wherein the ligands L ¹ and L ² are independently selected from the following structures: Wherein X, R ₁ , R ₂ , R ₃ and R ₄ are as defined in the first item of the patent application; Y represents O, S or NR ₂₄ ; R ₁₁ to R ₂₃ independently represent hydrogen, (C1- C60) alkyl, halogen, (C1-C60)alkyl having a halogen substituent, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecane, di C1-C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, di(C1-C30)alkylamino or di(C6-C30)arylamine: R ₁₃ to R ₁₆ and R ₁₇ to R ₂₀ may be bonded to an adjacent substituent via an alkylene or an extended alkenyl group, respectively, to form a fused ring; and the fused ring may further be selected from one or more selected from the group consisting of Substituted by a substituent: (C1-C60)alkyl, halogen, cyano, (C1-C60)alkyl having a halogen substituent, (C3-C60)cycloalkyl, (C1-C30) alkoxy, ( C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30) An arylalkyl group, a di(C1-C30)alkylamino group, and a di(C6-C30)arylamino group; R ₂₄ represents a (C1-C60)alkyl group or a (C6-C60)aryl group; and R ₁₁ The aryl or heteroaryl group to R ₂₄ can be further Substituted by one or more substituents selected from (C1-C60)alkyl, halo, cyano, (C1-C60)alkyl having a halogen substituent, (C3-C60)cycloalkyl, ( C1-C30) alkoxy, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryl An alkyl group, a tri(C6-C30)arylalkylene group, a di(C1-C30)alkylamino group, and a di(C6-C30)arylamino group. The electroluminescent device of claim 2, wherein the ligands L ¹ and L ² are independently selected from the following structures: Wherein X is as defined in the first item of the patent application; R ₁ to R ₇ independently represent hydrogen, (C1-C60)alkyl, halogen, (C1-C60)alkyl having a halogen substituent, and three (C1-C30)alkylalkyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl,(C6-C60)aryl, (C4- C60) a heteroaryl group, a di(C1-C30)alkylamino group or a di(C6-C30)arylamino group; R ₁₁ to R ₂₃ independently represent hydrogen, (C1-C60)alkyl, halogen, having (C1-C60)alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl (C6) -C30) arylalkyl, tris(C6-C30)aryldecyl, bis(C1-C30)alkylamino or bis(C6-C30)arylamine; R ₂₄ represents (C1-C60)alkane a group, (C6-C60) aryl or (C4-C60)heteroaryl; R ₂₅ to R ₃₂ independently represent hydrogen, (C1-C60)alkyl, halogen, cyano, having a halogen substituent (C1) -C60)alkyl, (C3-C60)cycloalkyl, (C1-C30)alkoxy, (C6-C60)aryl, (C4-C60)heteroaryl, tri(C1-C30)alkylnonane Base, di(C1-C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, di(C1-C3 0) an alkylamino group and a di(C6-C30)arylamino group; the aryl or heteroaryl group of R ₁ to R ₇ , R ₁₁ to R ₂₃ , R ₂₄ , and R ₂₅ to R ₃₂ may be further Substituted by one or more substituents selected from the group consisting of: (C1-C60)alkyl, halogen, cyano, (C1-C60)alkyl having a halogen substituent, (C3-C60)cycloalkyl, (C1 -C30) alkoxy, (C6-C60) aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryl A decyl group, a tris(C6-C30)aryldecylalkyl group, a di(C1-C30)alkylamino group, and a di(C6-C30)arylamino group. The electroluminescent device of claim 1, wherein M is a divalent metal selected from the group consisting of Be, Zn, Mg, Cu, and Ni, or a trivalent metal selected from the group consisting of Al, Ga, In, and B. The electroluminescent device of claim 1, wherein the Q system is selected from the following structures: The electroluminescent device of claim 1, wherein the organic layer comprises one or more compounds selected from the group consisting of arylamine compounds and styryl arylamine compounds. The electroluminescent device of claim 1, wherein the organic layer comprises one or more metals selected from the group consisting of: organometallics of Group 1, organometallics of Group 2, cycle 4 and The transition metal of the fifth cycle, the lanthanide metal and the d-transition elements. An electroluminescent device according to claim 1, which is an organic display, and further comprises a compound having an electroluminescence peak having a wavelength of not more than 560 nm in the organic layer. The electroluminescent device of claim 1, wherein the organic layer comprises an electroluminescent layer and a charge generating layer. The electroluminescent device of claim 1, wherein the inner surface of one or both of the pair of electrodes is provided with a mixed region of a reducing dopant and an organic substance, or an oxidative doping a mixed area of the agent and the organic substance. The electroluminescent device of claim 1, wherein in the electroluminescent region, the doping concentration of the electroluminescent dopant is from 1 to 20% by weight relative to the host material. A light-emitting diode comprising an organic electroluminescent compound represented by the chemical formula (1) and one or more electroluminescent dopants represented by the chemical formula (2): chemical formula (1) L ¹ L ² M(Q) _y chemical formula (2) M ¹ L ³ L ⁴ L ⁵ wherein the ligands L ¹ and L ² are independently selected from the following structures; Wherein M represents a divalent or trivalent metal; when M is a divalent metal, y is 0; and when M is a trivalent metal, y is 1; Q represents (C6-C60) aryloxy or tri (C6) -C60) arylalkylalkyl, and the aryloxy or triarylsulfanyl group of Q may be further substituted by (C1-C60)alkyl or (C6-C60)aryl; X represents O or S; ring A and Ring B is independently a 5- or 6-membered heteroaryl ring, or a 5- or 6-membered heteroaryl ring fused to a (C6-C60) aromatic ring; Ring A can form a chemical bond with R ₁ to form a fused ring, And Ring A or Ring B may be further substituted with one or more substituents selected from the group consisting of: (C1-C60)alkyl, halogen, halogen-substituted (C1-C60)alkyl, (C6-C60) aryl , (C4-C60)heteroaryl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl , a di(C1-C30)alkylamino group and a di(C6-C30)arylamino group; R ₁ to R ₇ independently represent hydrogen, (C1-C60)alkyl, halogen, having a halogen substituent ( C1-C60) alkyl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl, (C6- C60) aryl, (C4-C60) Group, di (C1-C30) alkylamino and di- (C6-C30) aryl group; or R ₁ to R ₇ may be respectively via an alkylene or alkenylene group linking to an adjacent substituent to form a fused And aryl or heteroaryl substituted on ring A or ring B, or the aryl or heteroaryl group of R ₁ to R ₇ or R ₁ to R ₇ via alkyl or alkenyl The fused ring bonded to an adjacent substituent may be further substituted with one or more substituents selected from the group consisting of: (C1-C60)alkyl, halogen, cyano, having a halogen substituent ( C1-C60)alkyl, (C3-C60)cycloalkyl, (C1-C30)alkoxy, (C6-C60)aryl, (C4-C60)heteroaryl, tri(C1-C30)alkyl矽alkyl, bis(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl, bis(C1-C30)alkylamino and bis(C6-C30)aryl An amino group; wherein the M ¹ group is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15, and Group 16 of the Periodic Table; The group, and the ligands L ³ , L ⁴ and L ⁵ are independently selected from the following structures: Wherein R ₆₁ to R ₆₃ independently represent a hydrogen (C1-C60) alkyl group having or not having a halogen substituent, and a (C6-C60) aryl group having or not having a (C1-C60) alkyl substituent; Or a halogen; R ₆₄ to R ₇₉ independently represent hydrogen, (C1-C60)alkyl, (C1-C30)alkoxy, (C3-C60)cycloalkyl, (C2-C30)alkenyl, ( C6-C60) aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, SF ₅ , tri(C1-C30)alkyldecyl, di(C1 -C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, cyano or halogen; or R ₇₀ to R ₇₆ may be alkyl (C2-C12) or C2-C12) an alkenyl group bonded to an adjacent substituent to form a fused or polyfused ring; and the alkyl, cycloalkyl, alkenyl or aryl group of R ₆₄ to R ₇₉ , or R ₇₀ and The fused or polycondensed ring formed by R ₇₆ via an alkyl or alkenyl linkage may be further subjected to one or more selected from the group consisting of (C1-C60)alkyl, (C6-C60)aryl, and the halogen substituents; R ₈₀ to R ₈₃ independently represent hydrogen system, with or without halogen substituent group of (C1-C60) alkyl, or with or without (C1-C60) alkyl substituted with The (C6-C60) aryl; R ₈₄ and R ₈₅ independently represent a hydrogen based, linear or branched chain (C1-C60) alkyl, (C6-C60) aryl or halogen; or R ₈₄ and R ₈₅ An alicyclic or monocyclic or polycyclic aromatic ring can be formed via a (C3-C12)alkylene group or a (C3-C12)alkylene group with or without a fused ring; and R ₈₄ and R ₈₅ The alicyclic ring or the monocyclic or polycyclic aromatic ring formed by the alkyl group, the aryl group or the R ₈₄ and R ₈₅ via a (C3-C12)alkylene group or a (C3-C12)alkylene group linkage. Further substituted with one or more substituents selected from the group consisting of a straight or branched chain (C1-C60) alkyl group with or without a halogen substituent, (C1-C30) alkoxy group, halogen, three (C1-C30)alkylalkylalkyl, tris(C6-C30)aryldecylalkyl, and (C6-C60)aryl; R ₈₆ represents (C1-C60)alkyl, (C6-C60)aryl, (C5 -C60)heteroaryl or halogen; R ₈₇ to R ₈₉ independently represent hydrogen, (C1-C60)alkyl, (C6-C60)aryl or halogen, and the alkyl or aryl of R ₈₆ to R ₈₉ The group may be further substituted by halogen or (C1-C60)alkyl; and z represents , or Wherein R ₁₀₁ to R ₁₁₂ independently represent hydrogen, (C1-C60)alkyl group having or without a halogen substituent, (C1-C30) alkoxy group, halogen, (C6-C60) aryl group, cyanide Or a (C5-C60)cycloalkyl group, or R ₁₀₁ to R ₁₁₂ may be bonded to an adjacent substituent via an alkyl or alkenyl group, respectively, to form a (C5-C7) spiro ring or a (C5-C9) thick Ring-bonded, or R ₁₀₁ to R ₁₁₂ may be bonded to R ₆₇ or R ₆₈ via an alkyl or alkenyl group to form a (C5-C7) fused ring.